What we've got here is failure to communicate.
Just missing out by one on making it into the top ten of the AFI list of the 100 most memorable American movie quotes of the first 100 years, this observation by the Captain is more than just an assertion made in a certain place at a certain time. It spans the entire decade which surrounds the film. Luke is quite specifically situated as an anti-establishment in rebellion with authority. Never mind that the actor playing him was just over 30 (the age over which nobody could be trusted at the time according to 60’s counterculture rules)…he was over 40! Didn’t matter. Luke was cool for no other reason than that he was in rebellion against convention, tradition and the Generation in which he found himself on the other younger side of the gap. (That other side being represented by an actor not even six years older, but that’s beside the point.)
He was a natural-born world-shaker.
Just in case you didn’t get the memo that Luke is more than just some nob given to making public displays of anger and outrage against conformity and regulation in the form of slicing off the tops of parking meters, Dragline puts everything into perspective at the end of the story. Luke’s non-conformity pushed beyond the chain gang. He was a world-shaker held in place by the shackles of authority.
Wish you’d stop being so good to me, Captain.
Proving that when it comes to the fascistic tendencies of authoritarians, non-conformists have to watch literally everything they say, this is the ironic observation that earns Luke a painful slap to the head. Communication is not the only thing fails the Captain; simple, intuitive awareness of right and wrong seems to be far beyond his ken.
Sometimes nothing can be a real cool hand.
Wonder what his nickname actually means? Think poker. Specifically, think winning a big poker pot that you collect and pull toward you with a severely busted hand. That you won by bluffing. By not even having a "hand" worth betting on.
I never planned anything in my life.
Now here’s a quote that could have been the tagline for the movie. The 1960’s counter-cultural non-conformists to which the movie was sublimely targeted would have picked up on this like a slogan covering their own life. Planning is for old people on the verge of retirement. Or at least those over 30.
Now just where I am supposed to fit in?
Keep in mind that Cool Hand Luke appeared the same year as Bonnie and Clyde and The Graduate. Because it stars a guy who had been around since the 1950s and a bunch of sweaty older guys, it can be hard for modern audiences to connect its seemingly already-outdated story of chain gangs to the swell of anti-establishment films that were being marketed so slickly to younger viewers at the time. And then you get to Luke’s wistful appeal to God to let him know exactly how his utterly meaningless and aimless life to that point fits into the big scheme of things. Then suddenly you realize that Luke belongs in the back of seat of the Clyde Barrow’s Ford or there on the back set between Benjamin and Elaine on that bus. It all comes together at this point.
